HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$122+ Cheap flights from Dulles Intl (IAD) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
IAD — SJU
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Dulles Intl to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Dulles Intl to Caribbean

Cheapest flights from Dulles Intl to Caribbean
Explore the most affordable flight options available from Dulles Intl to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:27 pm
IAD
-
SJU
1 stop6h 41m
Frontier
Tue 6/96:00 am
SJU
-
IAD
1 stop14h 02m
Frontier
Deal found 4/19$210
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:27 pm
IAD
-
SJU
1 stop6h 41m
Frontier
Sun 5/104:44 pm
SJU
-
IAD
1 stop22h 30m
Frontier
Deal found 4/20$211
This Frontier deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:27 pm
IAD
-
SJU
1 stop6h 41m
Frontier
Tue 5/126:00 am
SJU
-
IAD
1 stop11h 52m
Frontier
Deal found 4/21$212
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:27 pm
IAD
-
SJU
1 stop6h 41m
Frontier
Fri 6/53:03 am
SJU
-
IAD
1 stop15h 29m
Frontier
Deal found 4/20$214
This Trip.com deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/287:27 pm
IAD
-
SJU
1 stop6h 41m
Frontier
Mon 6/16:00 am
SJU
-
IAD
1 stop13h 50m
Frontier
Deal found 4/21$215
This Super.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:27 pm
IAD
-
SJU
1 stop27h 16m
Frontier
Sun 5/103:03 am
SJU
-
IAD
1 stop15h 39m
Frontier
Deal found 4/18$218
This Booking.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/315:30 pm
IAD
-
SJU
1 stop22h 25m
Frontier
Sat 6/66:00 am
SJU
-
IAD
1 stop13h 50m
Frontier
Deal found 4/18$219
This Kiwi.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:27 pm
IAD
-
SJU
1 stop6h 41m
Frontier
Wed 5/136:41 pm
SJU
-
IAD
2 stops21h 40m
Frontier
Deal found 4/18$221
This Trip.com deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/512:24 pm
IAD
-
SJU
1 stop11h 35m
Frontier
Sun 6/76:09 pm
SJU
-
IAD
1 stop24h 33m
Frontier
Deal found 4/18$222
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/153:59 pm
IAD
-
SJU
1 stop7h 58m
Frontier
Wed 5/207:30 am
SJU
-
IAD
2 stops36h 20m
Frontier
Deal found 4/20$224
This Priceline deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/310:02 am
IAD
-
SJU
1 stop23h 52m
Frontier
Fri 5/88:59 am
SJU
-
IAD
1 stop9h 43m
Frontier
Deal found 4/20$225
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:27 pm
IAD
-
SJU
1 stop12h 37m
Frontier
Wed 5/276:00 am
SJU
-
IAD
1 stop12h 42m
Frontier
Deal found 4/20$226

Find flight deals from Dulles Intl to Caribbean

Keep the following information in mind while searching for Dulles Intl to Caribbean flight deals. Data was last updated April 23, 2026.

Round-trip from

$210
(Kiwi.com)

One-way from

$122
(Kiwi.com)

Popular in

March

Cheapest in

July

Average price

$334

Good round-trip deal

$342 or less

Good one-way deal

$171 or less
From Washington, D.C. Dulles Intl to Caribbean
Search Deals
One-way flight from Washington, D.C. Dulles Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($18 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Washington, D.C. Dulles Intl to Caribbean.
Search Deals
Price to beat on a one-way flight from Washington, D.C. Dulles Intl to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Dulles Intl to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 23, 2026.
Use the filters below to find and compare flights from Washington, D.C. Dulles Intl Airport to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Washington, D.C.Saint Thomas Island

IAD - STT

IADSTT

Washington, D.C. Dulles Intl

Mon 5/4

6:00 am-2:48 pm

1 stop8h 48m

Saint Thomas Island Cyril E King

Wed 5/13

3:01 pm-12:51 am

1 stop9h 50m

$311

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Fri 5/15

5:24 pm-9:24 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Wed 5/20

4:55 pm-8:56 pm

Nonstop4h 01m

$347

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Thu 5/7

5:24 pm-9:24 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Thu 5/14

3:56 pm-12:33 am

1 stop8h 37m

$355

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Fri 7/3

10:16 am-8:43 pm

1 stop10h 27m

San Juan Luis Munoz Marin Intl

Wed 8/5

7:30 am-6:26 pm

1 stop10h 56m

$375
Quickest round-trip

Washington, D.C.San Juan

IAD - SJU

IADSJU

Washington, D.C. Dulles Intl

Sun 7/12

5:24 pm-9:24 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Tue 8/11

7:20 am-11:12 am

Nonstop3h 52m

$387

Washington, D.C.Simpson Bay

IAD - SXM

IADSXM

Washington, D.C. Dulles Intl

Fri 9/18

6:00 am-1:50 pm

1 stop7h 50m

Simpson Bay Princess Juliana

Mon 9/21

3:20 pm-12:10 am

1 stop8h 50m

$399

Washington, D.C.Simpson Bay

IAD - SXM

IADSXM

Washington, D.C. Dulles Intl

Wed 8/12

6:00 am-1:56 pm

1 stop7h 56m

Simpson Bay Princess Juliana

Wed 8/19

3:21 pm-12:10 am

1 stop8h 49m

$399

Washington, D.C.Willemstad

IAD - CUR

IADCUR

Washington, D.C. Dulles Intl

Mon 5/25

2:21 am-2:36 pm

1 stop12h 15m

Willemstad Hato Int.

Tue 6/2

1:23 pm-4:21 am

1 stop14h 58m

$401

Washington, D.C.Willemstad

IAD - CUR

IADCUR

Washington, D.C. Dulles Intl

Fri 5/15

6:08 am-2:01 pm

1 stop7h 53m

Willemstad Hato Int.

Fri 5/22

3:16 pm-12:51 am

1 stop9h 35m

$403

Washington, D.C.Willemstad

IAD - CUR

IADCUR

Washington, D.C. Dulles Intl

Fri 5/15

6:08 am-2:01 pm

1 stop7h 53m

Willemstad Hato Int.

Sun 5/17

3:16 pm-12:51 am

1 stop9h 35m

$403

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/18

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

Best time to book a flight from Dulles Intl to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Dulles Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Washington, D.C. Dulles Intl Airport to Caribbean

What is the cheapest month to book a flight from Washington, D.C. Dulles Intl Airport to Caribbean?

Currently, October is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Caribbean (average of $102). Flying from Washington, D.C. Dulles Intl Airport to Caribbean in August is currently the most expensive (average of $957). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from IAD to CB?

Find hourly flight availability from Dulles Intl to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 23, 2026.

A simple way to save on the total cost of your ticket is to fly from Washington, D.C. Dulles Intl Airport to Caribbean in the afternoon. If you’re flexible enough to do this you can expect to save up to 43% on your trip compared to booking a flight at noon.

What is the cheapest day to fly from Washington, D.C. Dulles Intl Airport to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from Dulles Intl to Caribbean. Price data was last updated on April 18, 2026.

Travelers seeking maximum savings on their Washington, D.C. Dulles Intl Airport to Caribbean flight should consider departing on Wednesday at noon when fares are most often at their lowest. Friday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Washington, D.C. Dulles Intl Airport to Caribbean

Explore weekly flight availability from Dulles Intl to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 23, 2026.

The most flights from IAD to 0CB are scheduled on a Monday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (5 on average).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated April 23, 2026.
Read reviews from past customers who have flown Delta,Copa Airlines, andUnited Airlines from Washington, D.C. Dulles Intl Airport to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,437 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.9

Overall

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,437 reviews
Delta
7.9
Good
8,437 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.9

Overall

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Copa Airlines
7.5
Good
1,580 reviews
Delta
7.9
Good
8,437 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.9

Overall

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,637 reviews
Delta
7.9
Good
8,437 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.9

Overall

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.1
Good
11,659 reviews
Delta
7.9
Good
8,437 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.9

Overall

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.7
Fair
2,981 reviews
Delta
7.9
Good
8,437 reviews

Food

7.2

Boarding

8.1

Crew

8.5

Comfort

7.9

Overall

7.9

Entertainment

7.8

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Dulles Intl to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Washington, D.C. Dulles Intl Airport to Caribbean?

    For as low as $347, Delta can have you in Caribbean from Washington, D.C. Dulles Intl Airport in 4h. The distance between Washington, D.C. Dulles Intl Airport and Caribbean is about 1573 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Washington, D.C. Dulles Intl Airport to Caribbean one-way?

    The cheapest airlines for a one-way flight from Washington, D.C. Dulles Intl Airport to Caribbean are Frontier ($59), United Airlines ($98), and Delta ($112).

  • What are the most popular routes from Washington, D.C. Dulles Intl Airport to Caribbean?

    The most popular flight routes from Washington, D.C. Dulles Intl Airport to Caribbean are Washington, D.C. Dulles Intl - San Juan Luis Munoz Marin Intl, Washington, D.C. Dulles Intl - Punta Cana and Washington, D.C. Dulles Intl - Oranjestad Reina Beatrix.

  • What are the most reliable airlines from Washington, D.C. Dulles Intl Airport to Caribbean?

    No one likes to see their flight delayed. When booking a flight from Washington, D.C. Dulles Intl Airport to Caribbean consider choosing United Airlines (90%), Air Canada (85%) or Brussels Airlines (82%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Washington, D.C. Dulles Intl Airport to Caribbean?

    While on average a flight from Washington, D.C. Dulles Intl Airport to Caribbean is generally $798, our data shows the cheapest flight currently is $164. When looking at the most popular route, (Washington, D.C. Dulles Intl - San Juan Luis Munoz Marin Intl), you can expect to pay $204 for that flight.

  • Can I find deals for flights from Dulles Intl to Caribbean that include hotel bookings?

    Yes. In addition to deals on Dulles Intl to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Dulles Intl to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Dulles Intl to Caribbean.

  • Can I find deals for business class flights from Dulles Intl to Caribbean?

    Yes. Cheapflights offers flight deals from Dulles Intl to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Washington, D.C. Dulles Intl Airport to Caribbean?

    Currently, October is the cheapest month in which you can book a flight from Washington, D.C. Dulles Intl Airport to Caribbean (average of $102). Flying from Washington, D.C. Dulles Intl Airport to Caribbean in August is currently the most expensive (average of $957). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Dulles Intl to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Dulles Intl to Dallas/Fort Worth flights
Baltimore to Dallas/Fort Worth flights
Dulles Intl to Seattle flights
Dulles Intl to Las Vegas flights
Reagan-National to Seattle flights
Dulles Intl to Miami flights
Dulles Intl to O'Hare Intl flights
Dulles Intl to Atlanta flights
Reagan-National to Los Angeles flights
Baltimore to Los Angeles flights
Baltimore to O'Hare Intl flights
Reagan-National to Miami flights
Baltimore to Atlanta flights
Dulles Intl to Orlando flights
Dulles Intl to Denver flights
Baltimore to Miami flights
Reagan-National to O'Hare Intl flights
Baltimore to Las Vegas flights
Reagan-National to Dallas/Fort Worth flights
Reagan-National to Las Vegas flights
Reagan-National to Atlanta flights
Reagan-National to Hobby flights
Reagan-National to Orlando flights
Dulles Intl to San Francisco flights
Baltimore to Orlando flights
Baltimore to Seattle flights
Dulles Intl to Los Angeles flights
Baltimore to Denver flights
Dulles Intl to Cancún flights
Baltimore to Fort Lauderdale flights
Dulles Intl to Hobby flights
Dulles Intl to Heathrow flights
Dulles Intl to Boston flights
Reagan-National to San Francisco flights
Baltimore to Boston flights
Baltimore to San Francisco flights
Dulles Intl to Luis Munoz Marin Intl flights
Reagan-National to Boston flights
Baltimore to Hobby flights
Baltimore to Heathrow flights
Dulles Intl to Tampa flights
Dulles Intl to New Orleans flights
Dulles Intl to Midway flights
Dulles Intl to Fort Lauderdale flights
Dulles Intl to George Bush Intcntl flights
Baltimore to Midway flights
Dulles Intl to Charles de Gaulle flights
Dulles Intl to Leonardo da Vinci/Fiumicino flights
Reagan-National to Fort Lauderdale flights
Dulles Intl to Sky Harbor Intl flights

Top 9 airlines flying from Dulles Intl to Caribbean

Discover the top 9 airlines that operate flights from Dulles Intl to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$91Average$429FlexibilityNo cancel feeOn-time62%
DeltaCheapest$136Average$563FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$151Average$249FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$161Average$552FlexibilityNo cancel feeOn-time62%
AviancaCheapest$162Average$382FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$189Average$425FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$225Average$592FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$238Average$518FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$251Average$615FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights